Identification

Name
Cefprozil
Accession Number
DB01150  (APRD00461)
Type
Small Molecule
Groups
Approved
Description

Cefprozil is a cephalosporin antibiotic. It can be used to treat bronchitis, ear infections, skin infections, and other bacterial infections.

Structure
Thumb
Synonyms
  • Cefprozil anhydrous
  • Cefprozilo
  • Cefprozilum
External IDs
BBS-1067 / BMY-28167
Product Ingredients
IngredientUNIICASInChI Key
Cefprozil monohydrate3ADV90MJVU121123-17-9ALYUMNAHLSSTOU-CIRGZYLNSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CefprozilPowder, for suspension250 mg/5mLOralPar Pharmaceutical Companies, Inc.2007-02-212007-02-21Us
CefprozilTablet500 mgOralPro Doc Limitee2009-06-102014-07-24Canada
CefprozilPowder, for suspension125 mg/5mLOralPar Pharmaceutical Companies, Inc.2007-02-212007-02-21Us
Cefprozil Powder for Oral SuspensionPowder, for suspension250 mgOralRanbaxy Inc.Not applicableNot applicableCanada
Cefprozil TabletsTablet500 mgOralRanbaxy Inc.Not applicableNot applicableCanada
Cefprozil TabletsTablet250 mgOralRanbaxy Inc.Not applicableNot applicableCanada
CefzilTablet250 mg/1OralCorden Pharma Latina S.p.A.2016-12-062016-12-23Us
CefzilTablet, film coated500 mg/1OralBristol Myers Squibb2009-06-012010-01-31Us
CefzilSuspension125 mg/5mLOralCorden Pharma Latina S.p.A.2016-12-062016-12-23Us
CefzilPowder, for suspension250 mg/5mLOralBristol Myers Squibb2009-06-012010-02-28Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-cefprozilTablet500 mgOralApotex Corporation2007-03-12Not applicableCanada
Apo-cefprozilTablet250 mgOralApotex Corporation2007-03-12Not applicableCanada
Apo-cefprozilPowder, for suspension250 mgOralApotex Corporation2007-04-20Not applicableCanada
Apo-cefprozilPowder, for suspension125 mgOralApotex Corporation2007-04-20Not applicableCanada
Auro-cefprozilTablet250 mgOralAuro Pharma Inc2012-01-13Not applicableCanada
Auro-cefprozilPowder, for suspension125 mgOralAuro Pharma Inc2012-01-132016-09-12Canada
Auro-cefprozilTablet500 mgOralAuro Pharma Inc2012-01-13Not applicableCanada
Auro-cefprozilPowder, for suspension250 mgOralAuro Pharma Inc2012-01-132016-09-12Canada
Ava-cefprozilTablet500 mgOralAvanstra Inc2011-10-112014-08-21Canada
Ava-cefprozilPowder, for suspension250 mgOralAvanstra Inc2011-10-112014-08-21Canada
International/Other Brands
Brisoral / Cefzil / Cronocef / Serozil
Categories
UNII
S1SDI2FJIY
CAS number
92665-29-7
Weight
Average: 389.426
Monoisotopic: 389.104541423
Chemical Formula
C18H19N3O5S
InChI Key
WDLWHQDACQUCJR-ZAMMOSSLSA-N
InChI
InChI=1S/C18H19N3O5S/c1-2-3-10-8-27-17-13(16(24)21(17)14(10)18(25)26)20-15(23)12(19)9-4-6-11(22)7-5-9/h2-7,12-13,17,22H,8,19H2,1H3,(H,20,23)(H,25,26)/b3-2+/t12-,13-,17-/m1/s1
IUPAC Name
(6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-8-oxo-3-(prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(C=CC)=C(N1C(=O)[C@@]2([H])NC(=O)[C@H](N)C1=CC=C(O)C=C1)C(O)=O

Pharmacology

Indication

For the treatment of the following infections (respiratory, skin, soft tissue, UTI, ENT) caused by; S. pneumoniae, H. influenzae, staphylococci, S. pyogenes (group A beta-hemolytic streptococci), E. coli, P. mirabilis, Klebsiella sp, coagulase-negative staph

Associated Conditions
Pharmacodynamics

Cefprozil, a semisynthetic, second-generation cephalosporin, is used to treat otitis media, soft-tissue infections, and respiratory tract infections.

Mechanism of action

Cefprozil, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefprozil interferes with an autolysin inhibitor.

TargetActionsOrganism
APenicillin-binding protein 1A
inhibitor
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
APenicillin-binding protein 2x
inhibitor
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
APenicillin-binding protein 2B
inhibitor
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Absorption

Oral bioavailability is approximately 95%.

Volume of distribution
  • 0.23 L/kg
Protein binding

36%

Metabolism

Cefprozil is eliminated primarily by the kidneys

Route of elimination
Not Available
Half life

1.3 hours

Clearance
  • 3 mL/min/kg [fasting subjects]
Toxicity

Single 5000 mg/kg oral doses of cefprozil caused no mortality or signs of toxicity in adult, weaning or neonatal rats, or adult mice. A single oral dose of 3000 mg/kg caused diarrhea and loss of appetite in cynomolgus monkeys, but no mortality.

Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Cefprozil is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Cefprozil is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Cefprozil is combined with 4-hydroxycoumarin.
AbacavirCefprozil may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseCefprozil may decrease the excretion rate of Acarbose which could result in a higher serum level.
AceclofenacCefprozil may decrease the excretion rate of Aceclofenac which could result in a higher serum level.
AcemetacinThe risk or severity of nephrotoxicity can be increased when Cefprozil is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Cefprozil is combined with Acenocoumarol.
AcetaminophenCefprozil may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
Acetylsalicylic acidThe risk or severity of nephrotoxicity can be increased when Acetylsalicylic acid is combined with Cefprozil.
Food Interactions
  • Take without regard to meals.

References

Synthesis Reference

Julia Greil, Johannes Ludescher, Siegfried Wolf, "Intermediates in cefprozil production." U.S. Patent US07355041, issued April 08, 2008.

US07355041
General References
Not Available
External Links
KEGG Compound
C06888
PubChem Compound
5281006
PubChem Substance
46504903
ChemSpider
4444481
ChEBI
3506
ChEMBL
CHEMBL276568
Therapeutic Targets Database
DAP000447
PharmGKB
PA164746342
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Cefprozil
ATC Codes
J01DC10 — Cefprozil
AHFS Codes
  • 08:12.06.08 — Second Generation Cephalosporins
FDA label
Download (203 KB)
MSDS
Download (44.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
1CompletedNot AvailableHealthy Volunteers2
1CompletedTreatmentHealthy Volunteers4
Not AvailableCompletedNot AvailableHealthy Volunteers2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Apotex Inc.
  • A-S Medication Solutions LLC
  • Aurobindo Pharma Ltd.
  • Bristol-Myers Squibb Co.
  • Dispensing Solutions
  • Greenstone LLC
  • Howard Beach Medical Equipment
  • Lupin Pharmaceuticals Inc.
  • Northstar Rx LLC
  • Orchid Healthcare
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Ranbaxy Laboratories
  • Redpharm Drug
  • Sandoz
  • Southwood Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
  • Wockhardt Ltd.
Dosage forms
FormRouteStrength
TabletOral500 mg
TabletOral500 mg/1
Powder, for suspensionOral125 mg/5mL
Powder, for suspensionOral250 mg/5mL
SuspensionOral125 mg/5mL
SuspensionOral250 mg/5mL
TabletOral250 mg/1
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral500 mg/1
Powder, for suspensionOral125 mg
Powder, for suspensionOral250 mg
TabletOral250 mg
Prices
Unit descriptionCostUnit
Cefprozil 250 mg/5ml Suspension 100ml Bottle78.86USD bottle
Cefzil 500 mg tablet6.6USD tablet
Cefprozil 500 mg tablet5.46USD tablet
Cefzil 250 mg tablet3.24USD tablet
Cefprozil 250 mg tablet2.7USD tablet
Apo-Cefprozil 500 mg Tablet1.99USD tablet
Ran-Cefprozil 500 mg Tablet1.99USD tablet
Sandoz Cefprozil 500 mg Tablet1.99USD tablet
Apo-Cefprozil 250 mg Tablet1.02USD tablet
Ran-Cefprozil 250 mg Tablet1.02USD tablet
Sandoz Cefprozil 250 mg Tablet1.02USD tablet
Cefzil 50 mg/ml Suspension0.35USD ml
Apo-Cefprozil 50 mg/ml Suspension0.2USD ml
Cefprozil 50 mg/ml Suspension0.2USD ml
Ran-Cefprozil 50 mg/ml Suspension0.2USD ml
Sandoz Cefprozil 50 mg/ml Suspension0.2USD ml
Cefzil 25 mg/ml Suspension0.18USD ml
Apo-Cefprozil 25 mg/ml Suspension0.1USD ml
Ran-Cefprozil 25 mg/ml Suspension0.1USD ml
Sandoz Cefprozil 25 mg/ml Suspension0.1USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)218-225 °CNot Available
water solubility55 mg/LNot Available
logP0.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.149 mg/mLALOGPS
logP0.94ALOGPS
logP-1.9ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)7.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.96 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity101.27 m3·mol-1ChemAxon
Polarizability39.35 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8478
Blood Brain Barrier-0.9962
Caco-2 permeable-0.8353
P-glycoprotein substrateSubstrate0.7853
P-glycoprotein inhibitor INon-inhibitor0.9315
P-glycoprotein inhibitor IINon-inhibitor0.9889
Renal organic cation transporterNon-inhibitor0.9264
CYP450 2C9 substrateNon-substrate0.8214
CYP450 2D6 substrateNon-substrate0.8324
CYP450 3A4 substrateSubstrate0.5102
CYP450 1A2 substrateNon-inhibitor0.8866
CYP450 2C9 inhibitorNon-inhibitor0.8768
CYP450 2D6 inhibitorNon-inhibitor0.9196
CYP450 2C19 inhibitorNon-inhibitor0.8825
CYP450 3A4 inhibitorNon-inhibitor0.8724
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8149
Ames testNon AMES toxic0.6562
CarcinogenicityNon-carcinogens0.8849
BiodegradationNot ready biodegradable0.9584
Rat acute toxicity1.6050 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9935
hERG inhibition (predictor II)Non-inhibitor0.7516
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Lactams
Sub Class
Beta lactams
Direct Parent
Cephalosporins
Alternative Parents
N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Phenylacetamides / 1-hydroxy-2-unsubstituted benzenoids / Aralkylamines / 1,3-thiazines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Amino acids / Azetidines
show 10 more
Substituents
Cephalosporin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Alpha-amino acid or derivatives / Phenylacetamide / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Aralkylamine / Meta-thiazine / Monocyclic benzene moiety
show 26 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
cephalosporin, semisynthetic derivative (CHEBI:3506)

Targets

Kind
Protein
Organism
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Penicillin binding
Specific Function
Cell wall formation.
Gene Name
ponA
Uniprot ID
Q04707
Uniprot Name
Penicillin-binding protein 1A
Molecular Weight
79757.96 Da
References
  1. Nagai K, Davies TA, Jacobs MR, Appelbaum PC: Effects of amino acid alterations in penicillin-binding proteins (PBPs) 1a, 2b, and 2x on PBP affinities of penicillin, ampicillin, amoxicillin, cefditoren, cefuroxime, cefprozil, and cefaclor in 18 clinical isolates of penicillin-susceptible, -intermediate, and -resistant pneumococci. Antimicrob Agents Chemother. 2002 May;46(5):1273-80. [PubMed:11959556]
Kind
Protein
Organism
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Penicillin binding
Specific Function
Penicillin-binding proteins (PBPs) function in the late steps of murein biosynthesis. Beta-lactams inactivate the PBPs by acylating an essential serine residue in the active site of these proteins.
Gene Name
pbpX
Uniprot ID
P14677
Uniprot Name
Penicillin-binding protein 2x
Molecular Weight
82312.475 Da
References
  1. Nagai K, Davies TA, Jacobs MR, Appelbaum PC: Effects of amino acid alterations in penicillin-binding proteins (PBPs) 1a, 2b, and 2x on PBP affinities of penicillin, ampicillin, amoxicillin, cefditoren, cefuroxime, cefprozil, and cefaclor in 18 clinical isolates of penicillin-susceptible, -intermediate, and -resistant pneumococci. Antimicrob Agents Chemother. 2002 May;46(5):1273-80. [PubMed:11959556]
Kind
Protein
Organism
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Penicillin binding
Specific Function
Not Available
Gene Name
penA
Uniprot ID
P0A3M5
Uniprot Name
Penicillin-binding protein 2B
Molecular Weight
73872.305 Da
References
  1. Nagai K, Davies TA, Jacobs MR, Appelbaum PC: Effects of amino acid alterations in penicillin-binding proteins (PBPs) 1a, 2b, and 2x on PBP affinities of penicillin, ampicillin, amoxicillin, cefditoren, cefuroxime, cefprozil, and cefaclor in 18 clinical isolates of penicillin-susceptible, -intermediate, and -resistant pneumococci. Antimicrob Agents Chemother. 2002 May;46(5):1273-80. [PubMed:11959556]

Drug created on June 13, 2005 07:24 / Updated on November 21, 2018 07:14